A resurgence of new HIV/AIDS cases among young men who have sex with men (YMSM; ages 18-24) underscores the importance of developing culturally and developmentally informed HIV/AIDS programs for YMSM. We propose to develop and pilot test a tailored, web-based intervention called MEET-ME that focuses on delivering HIV/AIDS prevention messages based on single YMSMs' relationship expectations and partner- seeking behaviors. To maximize intervention appeal and appropriateness, we will convene a youth advisory board (YAB) to provide insight and feedback during the intervention development process. Using an iterative design and development process, we will develop tailored messages that align YMSM's relationship experiences and desires with HIV/AIDS prevention strategies. We will then design and develop the MEET-ME tailored online prevention intervention, as well as an attention-control non-tailored HIV/AIDS prevention (NTHP) comparison intervention. After developing both interventions, we will use usability testing procedures to collect preliminary data from 16 YMSM on the proposed intervention's design and acceptability. Recommended changes will be added to the intervention prior to launching a small pilot randomized controlled trial (RCT). The pilot RCT will compare MEET-ME (N=120) to NTHP (N=60) to assess intervention feasibility and acceptability, and gather preliminary behavioral data to inform a subsequent application. Assessments will be collected at 30, 60, and 90 days follow-up. Specific Aims include: (1) To develop a tailored (MEET-ME) and non-tailored (NTHP) HIV/AIDS prevention intervention focused on addressing HIV/AIDS risk behaviors among single YMSM (ages 18-24); (2) To collect preliminary data on the feasibility, acceptability, and intervention content of the MEET-ME (N=16) in preparation for a small pilot RCT; and, (3) To implement a small pilot RCT of the refined MEET-ME (N=120) as compared to the NTHP (N=60) intervention, in order to evaluate its feasibility and acceptability and gather preliminary efficac results in reducing sexual risk behaviors.